Epoxidation of the commercially relevant divinylbenzene with [tetrakis-(pentafluorophenyl)porphyrinato]iron(III) chloride and its derivatives

Kainan Zhang, Ying Yu, Sonbinh T. Nguyen, Joseph T Hupp, Linda J. Broadbelt, Omar K. Farha

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Fluorinated Fe-porphyrins, especially [tetrakis(pentafluorophenyl)porphyrinato]iron(III) chloride (tetrakis(pentafluorophenyl)porphyrinato = TPFPP) (TPFPP)FeCl (Fepor-2a), were found to be highly efficient for catalyzing the double epoxidation of divinylbenzene (DVB) to divinylbenzene dioxide (DVBDO), a novel component of epoxy resin formulation. The electronic properties of the catalysts are highly dependent on the substituents on the phenyl groups of these metalloporphyrins. The electron-rich fluorinated Fe-porphyrins are more selective toward epoxidation but are more vulnerable toward decomposition in H2O2. On the other hand, the electron deficient Fe-porphyrins are more stable, yet more Lewis acidic, which facilitates the formation of byproducts such as epoxide ring opening and overoxidation.

Original languageEnglish
Pages (from-to)922-927
Number of pages6
JournalIndustrial and Engineering Chemistry Research
Volume54
Issue number3
DOIs
Publication statusPublished - Jan 28 2015

Fingerprint

divinyl benzene
Epoxidation
Porphyrins
Iron
Derivatives
Metalloporphyrins
Epoxy Resins
Electrons
Epoxy Compounds
Epoxy resins
Electronic properties
Byproducts
Decomposition
Catalysts
tetrakis(pentafluorophenyl)porphyrinato iron(III) chloride

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)
  • Industrial and Manufacturing Engineering

Cite this

Epoxidation of the commercially relevant divinylbenzene with [tetrakis-(pentafluorophenyl)porphyrinato]iron(III) chloride and its derivatives. / Zhang, Kainan; Yu, Ying; Nguyen, Sonbinh T.; Hupp, Joseph T; Broadbelt, Linda J.; Farha, Omar K.

In: Industrial and Engineering Chemistry Research, Vol. 54, No. 3, 28.01.2015, p. 922-927.

Research output: Contribution to journalArticle

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AU - Yu, Ying

AU - Nguyen, Sonbinh T.

AU - Hupp, Joseph T

AU - Broadbelt, Linda J.

AU - Farha, Omar K.

PY - 2015/1/28

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